I think we are in a similar situation. DH computer just crashed this weekend. We had an idea that it was coming and had purchased an external harddrive for him to back up his computer to, but we are unsure of our purchased i-tunes. Unfortunately, we have a lot because we have "i-tunes dates". We go get a $15 gift card and split it. We choose the music together. Basically, we spend an hour or so together looking at different music, but it is time together.